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Issue 11, 2015
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γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

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Abstract

A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

Graphical abstract: γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

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Publication details

The article was received on 09 Jan 2015, accepted on 28 Jan 2015 and first published on 29 Jan 2015


Article type: Paper
DOI: 10.1039/C5OB00050E
Citation: Org. Biomol. Chem., 2015,13, 3446-3456
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    γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

    Y. Jagadeesh, A. T. Tran, B. Luo, N. Auberger, J. Désiré, S. Nakagawa, A. Kato, Y. Zhang, M. Sollogoub and Y. Blériot, Org. Biomol. Chem., 2015, 13, 3446
    DOI: 10.1039/C5OB00050E

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